Sodium Hydroxide → 4-[3-(6-tert-Butyl-3-methyl-1-oxo-3,4-dihydro-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-1-methyl-1H-pyrrole-2-carboxylic acid amide

HRID 1025580ノート

反応式

HRID 1025580 の反応式
C([O:4][CH2:5][C:6]1[C:11]([C:12]2[CH:16]=[C:15]([C:17](=[O:19])[NH2:18])[N:14]([CH3:20])[CH:13]=2)=[CH:10][CH:9]=[CH:8][C:7]=1[N:21]1[N:30]([CH3:31])[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:27]=2)[C:22]1=[O:36])(=O)C.[OH-].[Na+]>O1CCCC1.C([O-])(O)=O.[Na+].ClCCl>[C:32]([C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][CH:25]=1)[C:22](=[O:36])[N:21]([C:7]1[C:6]([CH2:5][OH:4])=[C:11]([C:12]3[CH:16]=[C:15]([C:17]([NH2:18])=[O:19])[N:14]([CH3:20])[CH:13]=3)[CH:10]=[CH:9][CH:8]=1)[N:30]([CH3:31])[CH2:29]2)([CH3:35])([CH3:33])[CH3:34]

参加物

6

反応物 2

HCID 14798Sodium HydroxideHCID 710081532-(6-tert-butyl-3-methyl-1-oxo-3,4-dihydrophthalazin-2(1H)-yl)-6-(5-carbamoyl-1-methyl-1H-pyrrol-3-yl)benzyl acetate

生成物 1

HCID 710086164-[3-(6-tert-Butyl-3-methyl-1-oxo-3,4-dihydro-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-1-methyl-1H-pyrrole-2-carboxylic acid amide収率 99%

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
60 °C

実験手順

To 2-(6-tert-butyl-3-methyl-1-oxo-3,4-dihydrophthalazin-2(1H)-yl)-6-(5-carbamoyl-1-methyl-1H-pyrrol-3-yl)benzyl acetate (31 mg, 63.4 μmol, Eq: 1.00) in tetrahydrofuran was added NaOH (1.0 M (aqueous) 1.0 mL, 1.00 mmol, Eq: 15.8). The reaction mixture heated at 60° C. for 4 h. The mixture was cooled to room temperature. The solution was diluted with sat NaHCO3 (aqueous) and dichloromethane. The layers were separated. The aqueous layer was extracted once with dichloromethane. The organic extracts were combined and dried over MgSO4. The solution was filtered. Concentrated in vacuo to give 4-[3-(6-tert-Butyl-3-methyl-1-oxo-3,4-dihydro-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-1-methyl-1H-pyrrole-2-carboxylic acid amide (28 mg, 99%): 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.26-1.40 (m, 9H) 2.56 (s, 3H) 3.95 (s, 3H) 4.53 (br. s., 2H) 5.23 (s, 2H) 6.93 (d, J=1.89 Hz, 1H) 7.14 (d, J=1.89 Hz, 1H) 7.24-7.38 (m, 3H) 7.39-7.53 (m, 1H) 7.64 (dd, J=5.67, 3.40 Hz, 1H) 8.01 (d, J=8.31 Hz, 1H). LC/MS-ESI observed [M+H]+ 447.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted once with dichloromethane
  4. dry with materialdried over MgSO4
  5. filtrationThe solution was filtered
  6. concentrationConcentrated in vacuo

出典と根拠

ORDレコード
ord-608079c0574c45b88ec52367b57c731a
出典データセット
uspto-grants-2014_05
特許番号
US08729078B2

反応ノート

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